


Meet me in the Bar at 7...

by FR123



Category: Supernatural
Genre: Castiel & Sam Winchester Friendship, Fluff, M/M, Romance, cross-dressing, kinda sweet, not-cheating
Language: English
Status: Completed
Published: 2017-01-07
Updated: 2017-01-07
Packaged: 2018-09-15 14:35:06
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,150
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9239216
Author URL: https://archiveofourown.org/users/FR123/pseuds/FR123
Summary: Dean and Castiel have been dating for a while. Castiel wants to spice things up a bit in the bedroom and comes up with a fun little roleplaying game for Dean. If only he had warned Dean what the plan was....and maybe he should have told Sam too?





	

Dean entered the five star hotel lobby with a slight self-conscious sigh. He looked to the right and saw the entrance to the ‘State Trattoria Bar’. _Well this is a bit of a posh joint Cas_ he thought as he made his way over to the barstools. This was where Cas had told Dean to meet him.

 

_“... at 7.00pm tonight Dean. Don’t be late and make sure you dress nice!”_

_“I always dress nice!” Dean retorted with an affronted expression. Cas responded with a flat look, “Dean, I’ve been dating you for 2 years, I love you, but you own too much flannel.”_

_Dean opened his mouth to argue, then closed it again at Castiel’s raised eyebrow and pointed look at the clothes he was currently wearing._

_“Dean, please can you wear at least a shirt and suit pants?”_

So here Dean was, in his nice white shirt and black suit pants. He motions to the bartender, "Whisky, please", and takes a seat on one of the stools. He checks his phone, which has a background of both him and Castiel. The photo is of both of them sat on the hood of the impala, deans head is thrown back laughing at something Castiel had said and Castiel is looking at Dean with complete devotion and a large grin. The photo had been snapped by their best friend Charlie, as she is notorious for photographing everything. Dean smiled to himself remembering that day. 

 

Looking at the time, Dean realised that Cas was actually late, only by 15 minutes, but after being with the guy who turned up almost annoying early/on time to everything it was enough for dean to frown and give the door a quick glance.

 

Suddenly, Dean felt a presence at his side and he spun around on his seat, and was taken aback by the woman who was invading his personal space. He took in her appearance, she had on a pair of sunglasses and her mouth was highlighted by ruby red lipstick on her lips.

 

“Is this seat taken?” Her voice was quite deep, but Dean was used to Cas' gravelly voice, so it didn't really phase him. She was wearing a tight black dress that rode above her knees when she sat down. Her knowing smirk widened slightly before she asked “What's your name handsome?”

 

“Err it's Dean, look, I'm kindof waiting for someone so....”

 

“Oh, well they’re not here just yet, so we can get to know each other a little better.” She chuckled and leaned a little closer. Dean frowned and started to lean back, “I’m sorry, what exactly do you mean by that?”

 

 “Well, we can have a little fun before they get here right?” She smirked with her red painted lips.

 

Dean suddenly felt a bolt of fury flash through him, _how dare this woman assume that he would cheat?!_

“Look lady, I'm here waiting for my boyfriend, and I don't appreciate you coming over and assuming that I'm going to cheat on the man I love with you!” He sternly told her off. She looked really shocked and taken back by the outburst.

 

“Dean it's me.”

 

“What?”

 

She took off the shades and there were the gorgeous crystal blue eyes that Dean had fallen in love with.

 

“CAS?! What...but...I..huh?”

 

Castiel’s eyes were wide and filled with worry, “Dean, I'm sorry! I thought you recognised me! It was just meant to be a bit fun, I didn't mean to upset you!! I just – “ 

 

 “Cas breathe,” Dean cut off his boyfriend, “It's ok, just tell me what's going on?” He grabbed Cas’ hand and squeezed, Cas’ squeezed back.

 

“Well you know how a few weeks ago, we were talking about role playing? You know, like pretending we didn't know each other and picking each other up? And well, this was a bit of a surprise for you, but I've booked us a room here for the night and thought I'd invite you to the bar, I'd be here dressed like this and we could y’know, have a bit of fun...” He trails off, looking sad and ashamed, “I'm sorry dean, I really thought you had recognised me, and were just playing 'hard to get'. This was a stupid idea, let's just forget it and go, I'm sorry.” He starts to stand up, not meeting Dean’s eye.

 

“Hey, hey, wait a second. Yeah, ok maybe you could have given me a little warning!” Dean chuckles, “but if there is a room already paid for...” Dean raises his eyebrows as Castiel finally meets his eye again, “And I have to say Cas, I didn't realise just how good your legs would look I'm a dress.” He smirks and gives him leery look as Castiel flushes red, “Maybe we can still salvage this? Although, I have to say, I'm a little out of practice at picking people up!” He winks and Castiel starts to smile back. Castiel bites his bottom lip shyly, “Ok.”

 

Castiel takes a breath, “My name is Cassandra, what's yours?”

 

Dean smirks, “James, can I buy you a drink Cassandra?”

 

…....................................................

 

Sam Winchester was a lawyer for a large company and due to the fact that his company was in the middle of a multi-million dollar lawsuit he was having to work his Friday night, when he would much rather be at home with his wife Jess and their three Golden Retrievers.  

 

But no, instead he is here in a hotel lounge drinking scotch and smoozing some rich bigwig to get some information out of them to help with his aspect of the case. His client was wittering on about some expense when suddenly Sam heard a familiar laugh, one that he had been around since he was a child _What is Dean doing here?_

 

He spun his head around trying to see his brother, and he saw Dean at the bar with a woman? _That’s weird,_ Sam thought with a frown. Then Sam took in what was actually happening, due to growing up with Dean and spending many nights out at bars with his older brother during his formative teenage years, Sam was (Unfortunately he often used to think to himself) aware of how Dean operated when trying to ‘Chat up’ strangers.

 

But Sam had not witnessed Dean trying to pull anyone in years. Sam will never forget his brother admitting that he had met someone that he could actually see a future with. Before Castiel came into Dean’s life, Sam used to worry that his older brother would continue down the lonely route of one-night-stands and never meet anyone to spend his life with.

 

Which is why when he saw Dean at the bar apparently chatting up a woman, Sam felt like a bucket of cold water had been poured over him. Even as Sam was watching, Dean’s hand moved from her knee and started travelling slowly higher. Sam felt his jaw drop. _I don’t believe it, Dean is hopelessly and completely in love with Castiel! They have been together for years, what the hell are you playing at Dean? And Cas! This is going to destroy him. Although I might have to destroy Dean first, how could he do this?_ Sam was suddenly so angry at his brother he had to stop himself from storming across the room and punching him across the face.

 

“Mr Winchester?” Sam spun back around, the tone at which his client was using implied that he had been trying to get Sam’s attention for a few minutes. “Is there something wrong Mr Winchester?”

 

“Err...No, I'm sorry Mr Wesson, I thought I recognised someone.”

 

“I see, well as you know, I’m a very busy person, so if that's all for today I'll be off, it is the weekend after all!!

 

“Yes, of course Mr Wesson.” Sam was distracted as he stood to shake his client’s hand, “Thank you for all your help Sir, greatly appreciated.” 

 

As Mr Wesson turned and left the bar area, Sam took a seat where he could watch his brother at the bar with the mystery woman. As he watched the brunette with a pixie cut placed her hand on Dean’s shoulder and leaned in close to whisper in his ear. Dean’s eyebrows raised as he leaned towards her and a charming smile lit up his face as she finished whatever she was saying. Sam was furious, he watched as she got up and walked away, Dean was obviously checking her out as she sashayed away towards what Sam assumed were the restrooms. With a face like thunder, Sam stood up and started strinding towards his brother.

 

.......................................................

 

Dean stood with a smile on his face, downed the rest of his drink and turned around, only to nearly crash into his gargantuan of a little brother. “SAM?!” he spluttered, “What the hell are you doing? You scared the crap outta me!” Dean took a step back. 

 

Then he registered the look on Sam’s face, he was pissed, “What the hell am I doing? What the hell are you doing Dean?”

 

Dean wasn't even sure if he had seen Sam this angry before, he gave his brother a blank look.

 

“Huh?” was his intellectual reply.

 

“What are you doing with that woman? How could you cheat on Cas?”

 

 _Well kudos to Cas, his outfit has managed to fool both Winchester brothers in one night!_ Dean thought to himself. Then he smiled “Sam, it's really not what it looks like.”

 

That was apparently the wrong thing to say, Deans not sure if he has ever seen Sam as livid as he looked right then. He grabbed the front of Dean’s shirt with both hands and shook Dean.

 

“Are you kidding me?? Dean you’re all over that woman! I know you dean!! I watched for years as you picked up women... and men!! Your acting just like you did before you met Cas!! Don’t do this Dean, please, Cas is the best thing that’s ever happened to you!!”

 

“I know he’s the best thing that happened to me!” Dean retorted.

 

“Then fucking act like it!”

 

Dean took a deep breath, “Look Sam –“

 

“Sam?”

 

Both Winchester brothers stopped and turned to the new voice which came from Dean’s date.

 

Sam frowned in confusion, “How do you know my name?”

 

Dean’s dates had a surprised look on her face, and her wide blue eyes flitted between Sam and Dean.

 

“Can you put your brother down please?” Was the eventual reply she gave.

 

Sam was confused he released Dean from his grip, “Wait, what’s going on? How do you know who I am?” He turned to look directly at the woman and finally caught her eye....her familiar crystal.. blue... eyes....”OH MY GOD! Oh my god!! CAS??..........What the hell?”

 

Dean was trying to hold in a laugh as he answered his brother, “Well I told you it’s not what it looked like Sammy!” He clapped Sam on the shoulder with one hand.

 

“What is happening?”

 

Castiel was biting his bottom lip, “Sam, it just...I mean, it was just, err... you see Sam we –“

 

“Look Sam, a few weeks ago, me and Cas were having a chat about spicing things up in the bedroom –“

 

“Oh my god!”

 

Dean continues, “Well

 

Dean continued, “Well Cas came up with the idea for a roleplay, I admit I didn’t recognise him when I got here and he started to come onto me.” Dean chuckled at Sam’s disgusted look.

“I hope your happy, I nearly screwed up an important meeting to interrupt one of your kinky sex games!!”

“Hey, I’m the one that should be insulted! You thought I was cheating on Cas!!”

Sam gaped a Dean for a second, “Your right, I’m sorry Dean, I should have know you wouldn’t, but I just – “

“It’s ok Sam, it’s actually kind of sweet.” Castiel finally spoke out.

“What?? How the hell is thinking that I’m a cheating whore, sweet?!” Dean retorted with an indignant look on his face.

Cas looked at Dean, “Well he was trying to ‘defend my honor’,” he turned to the taller Winchester brother, “Thank you Sam, but neither me nor Dean are at risk of infidelity, but I can’t make any promises about ‘kinky sex games’ as you called them.” In Castiel’s usual bluntness.

“Oh my god, you know what? I don’t want to know! I’m glad your both fine. But I’m going home to my wife! Goodnight both of you.” Sam turned and marched out of the hotel.

Dean and Castiel looked at each other for a long moment before breaking out into giggles.

“Well, not that we’ve suitably traumatised my little brother, I do believe you said you have a room booked ‘Cassandra’.”

Castiel smirked, “It’s on the third floor,” he took Dean’s hand, “Let’s go get the elevator.” They started walking out of the bar with their hand entwined.

**Author's Note:**

> So, this is the first time I have EVER written any type of story in my life. I would really like to get some feedback as I have an idea for a much longer multi-chaptered story. Hope you all enjoyed this one!


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